Tennessee’s next trial court judge might be a prison company executive who has less courtroom experience than most inmates.

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In October 2000, Dick Cheney faced off for a debate with Connecticut Sen. Joseph Lieberman. The 60-year-old Cheney appeared comfortable discussing the ins and outs of policy and made good-natured jokes about Lieberman’s singing abilities, or lack thereof. Cheney’s smooth performance reflected his many years in public service. But the aspiring vice president also had a strong debate-preparation team made up of longtime friends and GOP loyalists. Among them was Gustavus Adolphus Puryear IV, a legislative director for Tennessee senator Bill Frist, who was on contract with the Bush/Cheney campaign. Puryear apparently did such a good job prepping Cheney that he was called in again in 2004 to help him gear up for his debate with Democratic vice-presidential candidate John Edwards.

Puryear’s efforts on behalf of the Bush administration paid off last June when the president nominated him to be a federal trial court judge for the Middle District of Tennessee. Puryear certainly isn’t the first judicial nominee selected primarily for his political service, but still, his resume is remarkably thin on the practice of law, a basic prerequisite even for the best-connected political hacks.

Puryear got his start in politics in the mid-1990s working as counsel to the Senate Committee on Governmental Affairs, then chaired by Fred Thompson, as it investigated the Clinton fundraising scandals. From there he went to work for Frist. Beyond a brief stint in private practice for a corporate law firm when he was fresh out of law school, Puryear has spent more time inside an executive suite than a courtroom. And it’s that corporate work that makes him an especially questionable candidate for the federal bench.

Puryear was in Washington last week for his confirmation hearing before the Senate Judiciary Committee, where Senators Arlen Specter (R.-Pa,) and Dianne Feinstein (D.-Ca.) both put his resume under a microscope, noting his conspicuous lack of trial experience. At one point Specter asked him point blank, “How many cases have you actually tried?” To which Puryear answered: Two. Indeed, according to his written questionnaire for the committee, of the two cases he has tried in the entirety of his legal career, he was lead counsel on one of them. The last time he litigated a case in federal court was more than a decade ago.

Puryear has spent the bulk of his legal career at the Tennessee-based Corrections Corporation of America, the nation’s largest private prison company. As its general counsel since 2001, Puryear has made millions of dollars working for a company that profits from the country’s incarceration boom, particularly through his recent sale of more than $3 million worth of the company’s stock. (His financial disclosure form shows a net worth of more than $13 million.) His employer creates enormous conflicts for Puryear as a potential federal judge, as the CCA gets sued all the time, often in the very district where he hopes to preside as judge. Since 2000, roughly 260 cases have been filed in that court against the CCA, its officers, and subsidiaries.

In addition, Puryear’s current job involves overseeing the CCA’s defense against inmate litigation, a prison staple that he has publicly dismissed as a nuisance, even though such litigation has led to significant verdicts and settlements against the company. For instance, in 2000, a South Carolina jury hit the CCA with a $3 million verdict for abusing juveniles. Other successful suits have alleged that the company’s employees abused inmates and provided negligent medical care. Yet in a quote he no doubt now regrets, in 2004 Puryear said that, “Litigation is an outlet for inmates. It’s something they can do in their spare time.” Inmate lawsuits typically account for more than 10 percent of the docket in Tennessee’s Middle District, meaning that Puryear will see his share of them if he gets confirmed.

During his confirmation hearing last week, Puryear told the committee that he would recuse himself from any cases involving the CCA—at least, he said, for some time after he’s divested all of his stock in the company. He dismissed concerns about his conflict of interest by noting that the CCA cases make up a small part of the court’s workload and that his recusals would not create problems for the other judges. But his promises to recuse still don’t get to the heart of a fundamental conflict: To the CCA, inmates are a revenue stream warehoused at the cheapest price. This not exactly the view of the criminal justice system you want from a judge if you are a defendant.

A trial court judge in Tennessee’s Middle District can expect to handle more than 60 criminal cases a year. Every person Puryear sends to prison is a potential money-maker for his former employer, which contracts with the federal government to manage 15 detention facilities, and also holds federal prisoners in other CCA institutions that house state and local prisoners when the need arises, according to Steve Owen, the company’s director of marketing and communications. The number of inmates coming from Tennessee may be relatively small, but still, it seems fair to ask whether Puryear’s conflict of interest runs so deep that he might have to recuse himself from criminal cases entirely.

Thus far, Puryear has largely escaped media scrutiny, as the activist groups that monitor the federal courts tend to focus mostly on appellate courts and the occasional Supreme Court battle rather than on trial court nominees. Puryear’s CV also doesn’t signal fights on many of the hot-button social issues that usually set off a confirmation battle. He doesn’t sound—or look—like Robert Bork. He’s young, patrician, a model member of the exclusive Belle Meade Country Club, and director of the Antiques & Garden Show of Nashville. But for his deep voice he could be Niles on “Frasier.” Nonetheless, Puryear might be in for an unexpected fight, due in part to his decision to publicly dis jailhouse lawyers.

Alex Friedmann was one of those jailhouse lawyers. He spent six years inside one of the CCA’s prisons in Tennessee for attempted murder and armed robbery. Friedmann actually sued the CCA while incarcerated for retaliating against him for his comments to a reporter for The Nation. Representing himself, he took another case all the way to a jury trial, where he mostly lost, though he won a default judgment against a former unit manager. He also appealed a different case against the state, over censorship, that went all the way to the Sixth Circuit court of appeals where he won. “In that regard, I’m more qualified than [Puryear] is,” he observes, noting that Puryear isn’t even admitted to practice in the Sixth Circuit.

Now out of prison nine years, Friedmann is an editor for Prison Legal News, which is how he first learned about Puryear’s nomination. After doing a little checking on him, Friedmann ran across Puryear’s quote about inmate litigation, which didn’t sit too well with him, and he set out to torpedo Puryear’s nomination. As a former CCA inmate and a board member of a Florida nonprofit group that opposes prison privatization, Friedmann readily admits that he’s not a disinterested party in the nomination battle. Nonetheless, his political instincts are sound. He is cobbling together a coalition to oppose Puryear’s nomination, including the American Federal State and Municipal Employees Union, which opposes private prisons for their anti-labor positions. Friedmann’s currently at work trying to enlist the real powerhouse of liberal judicial activists to join the coalition: women’s groups.

Friedmann has compiled stats from the federal court docket on the CCA’s lawsuit history in order to highlight the potential conflicts of interest Puryear might face, and he picked apart Puryear’s resume and his responses to the Senate Judiciary Committee’s questions last week. For instance, when pressed on his view of criminal defendants and prison inmates, Puryear pointed to his service as a commissioner on the National Prison Rape Elimination Commission. Skeptical, Friedmann checked out Puryear’s attendance record with the commission. He says the commission held eight public hearings between 2005 and 2007—and Puryear missed at least four of them. “If the gentleman does have a genuine concern about inmates, why did he miss half the meetings?” he asks.

Friedmann is also raising significant questions about Puryear’s response to questions about the death of a female inmate at the CCA’s facility in Nashville. The medical examiner ruled that 34-year-old Estelle Richardson was beaten to death while in the company’s custody. She suffered a skull fracture, broken ribs, and liver damage. Prosecutors indicted four CCA guards in 2005, but later dropped the charges after being unable to determine the time of death. So far, no one has been held responsible for Richardson’s death, although the CCA settled a private lawsuit filed by her family.

When Sen. Feinstein asked Puryear about the case, Puryear disputed the medical examiner’s findings and claimed that Richardson’s death might not have been a homicide at all. He suggested that the broken ribs and liver injury may have been caused by CPR. It’s “common” for people to suffer such injuries from CPR, Puryear said, to which a dumbfounded Feinstein exclaimed, “Common?” Apparently not satisfied with Puryear’s answers, Feinstein asked him to provide the committee with further written information about the case.

Meanwhile, after the hearing, Friedmann called the Tennessee medical examiner who worked the case, who he says reaffirmed the original finding that Robinson’s death was a homicide and that there was nothing to suggest her injuries were caused by resuscitation efforts. Friedmann also spoke with the lawyers who represented Richardson’s family and he says that they told him that the CCA never raised CPR injuries as a defense in the litigation. Puryear’s comments to the committee, says Freidmann, are “not supported by the medical record,” which makes him skeptical about Puryear’s judgment as a lawyer—and his credibility.

Friedmann seems to recognize that prison inmates are not the stuff of judicial confirmation fights, so he has also homed in on another issue that might provide more traction, not to mention the interest of powerful women’s groups: Puryear’s country club.

The tony Belle Meade Country Club in Nashville is so exclusive that you have to be a member just to access its website. It didn’t admit a single black member until 1994, a racist history so potent that even Puryear’s mentor, former Senate Majority Leader Bill Frist, quit the club in 1993 when he first ran for office. While Belle Meade admits women, Friedmann has heard that it still won’t give “lady members” voting rights. (Troy Cunningham, the controller of the club for the past 17 years, wouldn’t respond to questions about women’s voting rights, saying that “all questions flow through the members,” meaning that someone will have to put the question to Puryear himself.) But if Friedmann can stir up controversy over Puryear’s country club membership, he might actually have a shot at scuttling his nomination.

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